Woodstock competition offers $30,000 prize for best business idea

Cliff Johnson, left, and Larry Niles, two of Startup Woodstock’s organizers, hope to spur new business. Photo by Ethan Weinstein/VTDigger

WOODSTOCK — Let the best business win.

With $30,000 in seed money, three Woodstock business leaders helped create Startup Woodstock, a competition that will help launch a new business.

“The idea is, the closer the company is to solving a critical need within the community, that’s a big plus,” says Cliff Johnson, one of Startup Woodstock’s organizers and judges.

Johnson moved with his family from Atlanta to Woodstock during the pandemic. Over a decade ago, while working in Portland, Oregon, he founded Vacasa, an international vacation rental management company, which he left in 2018.

Johnson organizes the Woodstock competition with Jon Spector and Larry Niles, both members of the town’s Economic Development Commission, which focuses on issues such as housing, child care and downtown revitalization. The commission provided $10,000 for the contest, and the additional $20,000 came from private donors.

“We really want people to come here,” Niles said. “We’re going to do everything we can to solve some of these very obvious problems, or barriers, to opening a business.”

High rents downtown add to the barriers, Niles said, along with the perception that Woodstock has a difficult bureaucracy for would-be business owners. While the former may be true, he refuted the latter, saying almost all of the business owners interviewed by the commission reported having positive experiences with local government.

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Niles also rejects the idea that Woodstock only caters to a certain clientele.

“I always cringe at the thought that we’re just a rich town,” he said, “because we’re made up of a lot of merchants and a lot of people who have lived here all their lives.”

With that in mind, Niles and Johnson said Startup Woodstock hopes to cast a wide net in recruiting potential applicants for the prize money. People whose ideas may still be in their infancy are invited to apply. So are service-based businesses such as electrical, landscaping and childcare companies.

“A $30,000 grant can pretty easily help someone start a new child care business,” Johnson said.

The competition’s criteria require the business to fill an unmet gap in the community and hopefully create a living wage job or a sustainable owner-managed business.

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If successful, Johnson said he hopes the competition will “create a culture of entrepreneurship and (allow) people to create their own destiny.”

Johnson imagines that kind of culture could grow in Woodstock. He moved to Vermont to raise his family, and enjoys Woodstock’s school system, tight-knit community, and access to the outdoors. He works remotely, and sees the Windsor County vacation destination as a draw for more remote workers like him.

For a town of only about 3,000 people, Woodstock devotes considerable resources to economic development. Since 2016, the town’s Economic Development Commission has awarded more than $1 million in grants that support events, physical infrastructure, marketing and other initiatives.

This year, the town government created a program that pays landlords to convert short-term rentals to long-term rentals. The program aims to alleviate the town’s housing shortage, which has been made more acute by the town’s appeal to tourists. Property owners received $3,000 if they agreed to a one-year lease with a tenant, and $7,000 for a two-year lease.

Johnson acknowledged “concerns that come when a community has more vacation rentals coming in,” including through Vacasa, and added that short-term rentals can be a “minor contributing factor to housing affordability.”

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Still, he believes vacation rentals can be a “positive part of most communities” when they are licensed, taxed and follow local regulations.

Although it’s a new idea, Startup Woodstock could grow if it proves successful, according to organizers. Applicants can apply until Dec. 1, at which time a panel of judges to be announced will narrow the field to a group of finalists by Dec. 15. Those finalists will pitch their ideas in February, and a winner will be chosen shortly thereafter.

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